Sulphonylaminocarbonyltriazolinones

ABSTRACT

Herbicidal sulphonylaminocarbonyltriazolinones of the formula ##STR1## in which R 1  represents hydrogen, hydroxyl or amino, or represents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aryl, alkoxy, alkenyloxy, alkylamino and dialkylamino, 
     R 2  represents hydrogen, hydroxyl, mercapto or amino, or represents an optionally substituted radical from the series comprising alkyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, alkoxy, alkylamino and dialkylamino, and 
     R 3  represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl and heteroaryl, 
     and salts thereof. Intermediates of the formula ##STR2## in which A 1  represents in each case optionally substituted alkyl, alkenyl, cycloalkyl, alkoxy or dialkylamino and 
     A 2  represents hydrogen, or represents in each case optionally substituted alkyl, cycloalkyl, aralkyl, aryl or alkoxy, 
     provided that both A 1  and A 2  do not simultaneously represent alkyl, are also new.

This is a division of application Ser. No. 816,365, filed Dec. 30, 1991, now U.S. Pat. No. 5,241,074, which is a division of application Ser. No. 692,439, filed Apr. 29, 1991, now U.S. Pat. No. 5,094,683, which is a division of application Ser. No. 556,052, filed Jul. 20, 1990, now U.S. Pat. No. 5,057,144, which is a c-i-p of application Ser. No. 337,775, filed Apr. 13, 1989, now abandoned.

The invention relates to new sulphonylaminocarbonyltriazolinones, to several processes for their preparation, and to their use as herbicides.

It is known that certain substituted aminocarbonylimidazolinones, such as, for example, 1-isobutylaminocarbonyl-2-imidazolidinone (isocarbamide), have herbicidal properties (cf. R. Wegler, Chemie der Pflanzenschutz-und Schadlingsbekampfungsmittel [Chemistry of Plant Protection Agents and Pesticides], Vol. 5, p. 219, Springer-Verlag, Berlin-Heidelberg-New York, 1977). However, the action of this compound is not satisfactory in all respects. The new sulphonylaminocarbonyl-triazolinones of the general formula (I) ##STR3## in which R¹ represents hydrogen, hydroxyl or amino, or represents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aryl, alkoxy, alkenyloxy, alkylamino and dialkylamino,

R² represents hydrogen, hydroxyl, mercapto or amino, or represents an optionally substituted radical from the series comprising alkyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, alkoxy, alkylamino and dialkylamino, and

R³ represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl and heteroaryl,

as well as salts of compounds of the formula (I), have now been found.

The new sulphonylaminocarbonyltriazolinones of the general formula (I) are obtained when

a) triazolinones of the general formula (II) ##STR4## in which R¹ and R² have the abovementioned meanings, are reacted with sulphonyl isocyanates of the general formula (III)

    R.sup.3 --SO.sub.2 --N═C═O                         (III)

in which

R³ has the abovementioned meaning, if appropriate in the presence of a diluent, or when

b) triazolinone derivatives of the general formula (IV) ##STR5## in which R¹ and R² have the abovementioned meanings and

Z represents halogen, alkoxy, aralkoxy or aryloxy, are reacted with sulphonamides of the general formula (V)

    R.sup.3 --SO.sub.2 --NH.sub.2                              (V)

in which

R³ has the abovementioned meaning, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or when

c) triazolinones of the general formula (II) ##STR6## in which R¹ and R² have the abovementioned meanings are reacted with sulphonamide derivatives of the general formula (VI)

    R.sup.3 --SO.sub.2 --NH--CO--Z                             (VI)

in which

R³ has the abovementioned meaning and

Z represents halogen, alkoxy, aralkoxy or aryloxy, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, and, if appropriate, salts are formed by customary methods from the compounds of the formula (I) prepared by process (a), (b) or (c).

The new sulphonylaminocarbonyltriazolinones of the general formula (I) and their salts are distinguished by a powerful herbicidal activity. Surprisingly, the new compounds of the formula (I) show a considerably better herbicidal action than the known herbicide 1-isobutylaminocarbonyl-2-imidazolidinone (isocarbamide), which has a similar structure.

The invention preferably relates to compounds of the formula (I) in which

R¹ represents hydrogen, hydroxyl or amino, or represents C₁ -C₆ -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylcarbonyl or C₁ -C₄ -alkoxy-carbonyl, or represents C₃ -C₆ -alkenyl or C₃ -C₆ -alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents C₃ -C₆ -cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or C₁ -C₄ -alkyl, or represents phenyl-C₁ -C₃ -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy and/or C₁ -C₄ -alkoxy-carbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy, fluorine- and/or chlorine-substituted C₁ -C₃ -alkoxy, C₁ -C₄ -alkylthio, fluorine- and/or chlorine-substituted C₁ -C₃ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl and/or C₁ -C₄ -alkoxycarbonyl, or represents C₁ -C₆ -alkoxy which is optionally substituted by fluorine, chlorine, cyano, phenyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxy-carbonyl, or represents C₃ -C₄ -alkenyloxy, or represents C₁ -C₄ -alkylamino which is optionally substituted by fluorine, cyano, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxy-carbonyl, or represents di-(C₁ -C₄ -alkyl)-amino,

R² represents hydrogen, hydroxyl, mercapto or amino, or represents C₁ -C₆ -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C₃ -C₆ cycloalkyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxy-carbonyl, or represents C₃ -C₆ -cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or C₁ -C₄ -alkyl, or represents cyclohexenyl, or represents phenyl-C₁ -C₃ -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy and/or C₁ -C₄ -alkoxy-carbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy, fluorine- and/or chlorine-substituted C₁ -C₃ -alkoxy, C₁ -C₄ -alkylthio, fluorine- and/or chlorine-substituted C₁ -C₃ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl and/or C₁ -C₄ -alkoxycarbonyl, or represents C₁ -C₆ -alkoxy which is optionally substituted by fluorine, chlorine, cyano, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxy-carbonyl, or represents C₁ -C₄ -alkylamino or di-(C₁ -C₄ -alkyl)-amino, and

R³ represents the group ##STR7## where R⁴ and R⁵ are identical or different and represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, C₁ -C₆ -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylamino-carbonyl, di( C₁ -C₄ -alkyl) amino-carbonyl, hydroxyl, C₁ -C₄ -alkoxy, formyloxy, C₁ -C₄ -alkyl-carbonyloxy, C₁ -C₄ -alkoxycarbonyloxy, C₁ -C₄ -alkylamino-carbonyloxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, di-(C₁ -C₄ -alkyl)-aminosulphonyl, C₃ -C₆ -cycloalkyl or phenyl), or represent C₂ -C₆ -alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl), or represent C₂ -C₆ -alkinyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl), or represent C₁ -C₄ -alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl), or represent C₁ -C₄ -alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl), or represent C₃ -C₆ -alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C₁ -C₄ -alkoxy-carbonyl), or represent C₂ -C₆ -alkenylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₃ -alkylthio or C₁ -C₄ -alkoxycarbonyl), C₃ -C₆ -alkinyloxy, C₃ -C₆ -alkinylthio, or represent the radical --S(O)_(p) --R⁶ where

P represents the numbers 1 or 2 and

R⁶ represents C₁ -C₄ -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano or C₁ -C₄ -alkoxy-carbonyl), C₃ -C₆ -alkenyl, C₃ -C₆ -alkinyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkoxy-C₁ -C₄ -alkylamino, C₁ -C₄ -alkylamino, di-(C₁ -C₄ -alkyl)-amino or phenyl, or represents the radical --NHOR⁷ where

R⁷ represents C₁ -C₁₂ -alkyl (which is optionally substituted by fluorine, chlorine, cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylamino-carbonyl or di-(C₁ -C₄ -alkyl)-aminocarbonyl), or represents C₃ -C₆ -alkenyl (which is optionally substituted by fluorine, chlorine or bromine), C₃ -C₆ -alkinyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₂ -alkyl, phenyl-C₁ -C₂ -alkyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxy-carbonyl), or represents benzohydryl, or represents phenyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy, C₁ -C₂ -fluoroalkoxy, C₁ -C₄ -alkylthio, trifluoromethylthio or C₁ -C₄ -alkoxycarbonyl),

R⁴ and/or R⁵ furthermore represent phenyl or phenoxy, or represent C₁ -C₄ -alkylcarbonylamino, C₁ -C₄ -alkoxycarbonylamino, C₁ -C₄ -alkylamino-carbonylamino, di-(C₁ -C₄ -alkyl) amino-carbonylamino, or represent the radical --CO--R⁸, where

R⁸ represents C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₃ -C₆ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₁ -C₄ alkylthio, C₁ -C₄ -alkylamino, C₁ -C₄ -alkoxyamino, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl-amino or di-(C₁ -C₄ -alkyl)amino (each of which is optionally substituted by fluorine and/or chlorine),

R⁴ and/or R⁵ furthermore represent trimethylsilyl, thiazolinyl, C₁ -C₄ -alkylsulphonyloxy, di-(C₁ -C₄ -alkyl)-aminosulphonylamino, or represent the radical --CH═N--R⁹, where

R⁹ represents C₁ -C₆ -alkyl which is optionally substituted by fluorine, chlorine, cyano, carboxyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl, or represents benzyl which is optionally substituted by fluorine or chlorine, or represents C₃ -C₆ -alkenyl or C₃ -C₆ -alkinyl, each of which is optionally substituted by fluorine or chlorine, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, or represents C₁ -C₆ -alkoxy, C₃ -C₆ -alkenoxy, C₃ -C₆ -alkinoxy or benzyloxy, each of which is optionally substituted by fluorine and/or chlorine, or represents amino, C₁ -C₄ -alkylamino, di-(C₁ -C₄ -alkyl)-amino, phenylamino, C₁ -C₄ -alkyl-carbonyl-amino, C₁ -C₄ -alkoxy-carbonylamino or C₁ -C₄ -alkyl-sulphonylamino, or represents phenylsulphonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl,

furthermore

R³ represents the radical ##STR8## where R¹⁰ represents hydrogen or C₁ -C₄ -alkyl,

R¹¹ and R¹² are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), carboxyl, C₁ -C₄ -alkoxy-carbonyl, dimethylaminocarbonyl, C₁ -C₄ -alkylsulphonyl or di-(C₁ -C₄ -alkyl)-aminosulphonyl;

furthermore

R³ represents the radical ##STR9## where R¹³ and R¹⁴ are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine) or C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine);

furthermore

R³ represents the radical ##STR10## where R¹⁵ and R¹⁶ are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), or represent C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl (each of which is optionally substituted by fluorine and/or chlorine), or represent di-(C₁ -C₄ -alkyl)aminosulphonyl or C₁ -C₄ -alkoxy-carbonyl or dimethylaminocarbonyl;

furthermore

R³ represents the radical ##STR11## R¹⁷ and R¹⁸ are identical or different and represent hydrogen, fluorine, chlorine, bromine, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or bromine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), or represent C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl (each of which is optionally substituted by fluorine and/or chlorine), or represent di-(C₁ -C₄ -alkyl)-aminosulphonyl;

furthermore

R³ represents the radical ##STR12## where R¹⁹ and R²⁰ are identical or different and represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine), di-(C₁ -C₄ -alkyl)-amino-sulphonyl, C₁ -C₄ -alkoxy-carbonyl or dimethylaminocarbonyl, and

A represents oxygen, sulphur or the group N--Z¹,

where

Z¹ represents hydrogen, C₁ -C₄ -alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C₃ -C₆ -cycloalkyl, benzyl, phenyl (which is optionally substituted by fluorine, chlorine, bromine or nitro), C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxy-carbonyl or di-(C₁ -C₄ -alkyl)-aminocarbonyl;

furthermore

R³ represents the radical ##STR13## where R²¹ and R²² are identical or different and represent hydrogen, C₁ -C₄ -alkyl, halogen, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkoxy or C₁ -C₄ -halogenoalkoxy,

Y¹ represents sulphur or the group N--R²³, where

R²³ represents hydrogen or C₁ -C₄ -alkyl;

furthermore

R³ represents the radical ##STR14## where R²⁴ represents hydrogen, C₁ -C₄ -alkyl, benzyl, quinolinyl or phenyl,

R²⁵ represents hydrogen, halogen, cyano, nitro, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), dioxolanyl or C₁ -C₄ -alkoxy-carbonyl, and

R²⁶ represents hydrogen, halogen or C₁ -C₄ -alkyl;

furthermore

R³ represents one of the groups listed below, ##STR15##

The invention furthermore preferably relates to the sodium, potassium, magnesium, calcium, ammonium, C₁ -C₄ -alkylammonium, di-(C₁ -C₄ -alkyl)-ammonium, tri-(C₁ -C₄ -alkyl)-ammonium, C₅ - or C₆ -cycloalkyl-ammonium and di-(C₁ -C₂ -alkyl)-benzyl-ammonium salts of compounds of the formula (I) in which R¹, R² and R³ have the meanings mentioned above as being preferred.

In particular, the invention relates to compounds of the formula (I) in which

R¹ represents hydrogen, or represents C₁ -C₄ -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, methoxy or ethoxy, or represents allyl, or represents C₃ -C₆ -cycloalkyl, or represents phenyl, or represents benzyl, or represents C₁ -C₃ -alkoxy, or represents C₁ -C₃ -alkylamino, or represents di-(C₁ -C₂ -alkyl)-amino,

R² represents hydrogen, or represents C₁ -C₄ -alkyl which is optionally substituted by fluorine and/or chlorine or by methoxy or ethoxy, or represents C₃ -C₆ -cycloalkyl, or represents phenyl, or represents C₁ -C₃ -alkoxy, or represents C₁ -C₃ -alkylamino, or represents di-(C₁ -C₂ -alkyl)-amino, and

R³ represents the group ##STR16## where R⁴ represents fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-methoxyethoxy, C₁ -C₃ -alkylthio, C₁ -C₃ -alkylsulphinyl, C₁ -C₃ -alkylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylaminosulphonyl, phenyl, phenoxy or C₁ -C₃ -alkoxy-carbonyl, and

R⁵ represents hydrogen, fluorine, chlorine or bromine;

furthermore

R³ represents the radical ##STR17## where R¹⁰ represents hydrogen,

R¹¹ represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl, and

R¹² represents hydrogen;

furthermore

R³ represents the radical ##STR18## where R represents C₁ -C₄ -alkyl, or represents the radical ##STR19## where R represents C₁ -C₄ -alkyl.

Examples of the compounds according to the invention are listed in Table 1 below--cf. also the Preparation Examples. ##STR20##

                                      TABLE 1                                      __________________________________________________________________________     Examples of the compounds of the formula (I)                                   R.sup.1     R.sup.2   R.sup.3                                                  __________________________________________________________________________                 H                                                                                         ##STR21##                                                ##STR22##  H                                                                                         ##STR23##                                               CH.sub.2CHCH.sub.2                                                                         C.sub.2 H.sub.5                                                                           ##STR24##                                               OCH.sub.3   C.sub.3 H.sub.7                                                                           ##STR25##                                               OCH.sub.2CHCH.sub.2                                                                         ##STR26##                                                                                ##STR27##                                               C.sub.2 H.sub.5                                                                            C.sub.4 H.sub.9 -n                                                                        ##STR28##                                               CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR29##                                                ##STR30##  C.sub.3 H.sub.7                                                                           ##STR31##                                               CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR32##                                               C.sub.2 H.sub.5                                                                            C.sub.3 H.sub.7                                                                           ##STR33##                                               OC.sub.2 H.sub.5                                                                            ##STR34##                                                                                ##STR35##                                               OC.sub.3 H.sub.7                                                                           CH.sub.3                                                                                  ##STR36##                                               CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR37##                                               N(CH.sub.3).sub.2                                                                           ##STR38##                                                                                ##STR39##                                               NHCH.sub.3                                                                                  ##STR40##                                                                                ##STR41##                                               CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR42##                                                ##STR43##  OCH.sub.3                                                                                 ##STR44##                                                ##STR45##  OC.sub.2 H.sub.5                                                                          ##STR46##                                                ##STR47##                                                                                  ##STR48##                                                                                ##STR49##                                                ##STR50##  C.sub.3 H.sub.7                                                                           ##STR51##                                                ##STR52##  C.sub.3 H.sub.7                                                                           ##STR53##                                               CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR54##                                               CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR55##                                                ##STR56##  C.sub.3 H.sub.7                                                                           ##STR57##                                               CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR58##                                               C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                           ##STR59##                                                ##STR60##  C.sub.3 H.sub.7                                                                           ##STR61##                                               C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                           ##STR62##                                               CH.sub.3    C.sub.3 H.sub.7 -n                                                                        ##STR63##                                                ##STR64##  C.sub.3 H.sub.7 -n                                                                        ##STR65##                                                ##STR66##  CH.sub.3                                                                                  ##STR67##                                               CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR68##                                               CH.sub.3                                                                                    ##STR69##                                                                                ##STR70##                                               C.sub.2 H.sub.5                                                                             ##STR71##                                                                                ##STR72##                                               C.sub.3 H.sub.7                                                                            C.sub.3 H.sub.7                                                                           ##STR73##                                               CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR74##                                               CH.sub.3                                                                                    ##STR75##                                                                                ##STR76##                                               OCH.sub.3   C.sub.2 H.sub.5                                                                           ##STR77##                                               OC.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                           ##STR78##                                               CH.sub.3    CH.sub.3                                                                                  ##STR79##                                               CH.sub.3    C.sub. 2 H.sub.5                                                                          ##STR80##                                                ##STR81##                                                                                  ##STR82##                                                                                ##STR83##                                               CH.sub.3    CH.sub.3                                                                                  ##STR84##                                               CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR85##                                               OCH.sub.2CHCH.sub.2                                                                        C.sub.2 H.sub.5                                                                           ##STR86##                                               OCH.sub.3   C.sub.2 H.sub.5                                                                           ##STR87##                                               CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR88##                                               CH.sub.3    CH.sub.2CHCH.sub.2                                                                        ##STR89##                                               CH.sub.3    CH.sub. 2OCH.sub.3                                                                        ##STR90##                                               CH.sub.3    CH.sub.2OC.sub.2 H.sub.5                                                                  ##STR91##                                               C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.4OCH.sub.3                                                                  ##STR92##                                               CH.sub.2CHCH.sub.2                                                                         H                                                                                         ##STR93##                                               CH.sub.2CHCH.sub.2                                                                         CH.sub.3                                                                                  ##STR94##                                               CH.sub.2CHCH.sub.2                                                                         C.sub.2 H.sub.5                                                                           ##STR95##                                               C.sub.2 H.sub.5                                                                             ##STR96##                                                                                ##STR97##                                               CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR98##                                               NHCH.sub.3  C.sub.2 H.sub.5                                                                           ##STR99##                                               NHCH.sub.3                                                                                  ##STR100##                                                                               ##STR101##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR102##                                               ##STR103## CH.sub.3 H.sub.7                                                                          ##STR104##                                              .sub.2 H.sub.5                                                                             C.sub.4 H.sub.9                                                                           ##STR105##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR106##                                               ##STR107## C.sub.2 H.sub.5                                                                           ##STR108##                                              CH.sub.3                                                                                    ##STR109##                                                                               ##STR110##                                              C.sub.2 H.sub.5                                                                             ##STR111##                                                                               ##STR112##                                              OCH.sub.3   CH(CH.sub.3).sub.2                                                                        ##STR113##                                              OC.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                           ##STR114##                                              CH.sub.3    H                                                                                         ##STR115##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR116##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR117##                                              OCH.sub.3   C.sub.3 H.sub.7                                                                           ##STR118##                                              OCH.sub.3   H                                                                                         ##STR119##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR120##                                              CH.sub.2 CHCH.sub.2                                                                        CH.sub.2OCH.sub.3                                                                         ##STR121##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR122##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR123##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR124##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR125##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR126##                                              CH.sub.3    C(CH.sub.3).sub.3                                                                         ##STR127##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR128##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR129##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR130##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR131##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR132##                                              CH.sub.3    C(CH.sub.3).sub.3                                                                         ##STR133##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR134##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR135##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR136##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR137##                                              CH.sub.3    C(CH.sub.3).sub.3                                                                         ##STR138##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR139##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR140##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR141##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR142##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR143##                                              CH.sub.3    C(CH.sub.3).sub.3                                                                         ##STR144##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR145##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR146##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR147##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR148##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR149##                                              CH.sub.3    C(CH.sub.3).sub.3                                                                         ##STR150##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR151##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR152##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR153##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR154##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR155##                                              CH.sub.3    C(CH.sub.3).sub.3                                                                         ##STR156##                                              C.sub.2 H.sub.5                                                                            CH.sub.3                                                                                  ##STR157##                                              C.sub.3 H.sub.7                                                                            CH.sub.3                                                                                  ##STR158##                                              CH.sub.3    C(CH.sub.3).sub.3                                                                         ##STR159##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR160##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR161##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR162##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR163##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR164##                                              CH.sub.3    C(CH.sub.3).sub.3                                                                         ##STR165##                                              CH.sub.3    CH.sub.3                                                                                  ##STR166##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR167##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR168##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR169##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR170##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR171##                                              CH.sub.3    C(CH.sub.3).sub.3                                                                         ##STR172##                                              C.sub.2 H.sub.5                                                                            CH.sub.3                                                                                  ##STR173##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR174##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR175##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR176##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR177##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR178##                                              CH.sub.3    C(CH.sub.3).sub.3                                                                         ##STR179##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR180##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR181##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR182##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR183##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR184##                                              CH.sub.3    C(CH.sub.3).sub.3                                                                         ##STR185##                                              C.sub.2 H.sub.5                                                                            CH.sub.3                                                                                  ##STR186##                                              C.sub.3 H.sub.7                                                                            CH.sub.3                                                                                  ##STR187##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR188##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR189##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR190##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR191##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR192##                                              CH.sub.3    C(CH.sub.3).sub.3                                                                         ##STR193##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR194##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR195##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR196##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR197##                                              CH.sub.3    C(CH.sub.3).sub.3                                                                         ##STR198##                                              CH.sub.3    CH.sub.3                                                                                  ##STR199##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR200##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR201##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR202##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR203##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR204##                                              CH.sub.3    CH.sub.3                                                                                  ##STR205##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR206##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR207##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR208##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR209##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR210##                                              CH.sub.3    C(CH.sub.3).sub.3                                                                         ##STR211##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR212##                                              CH.sub. 3   C.sub.3 H.sub.7                                                                           ##STR213##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR214##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR215##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR216##                                              CH.sub.3    C(CH.sub.3).sub.3                                                                         ##STR217##                                              CH.sub.3    CH.sub.3                                                                                  ##STR218##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR219##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR220##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR221##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR222##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR223##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR224##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR225##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR226##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR227##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR228##                                              CH.sub.3    C(CH.sub.3).sub.3                                                                         ##STR229##                                              CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR230##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR231##                                              CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR232##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR233##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR234##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR235##                                              CH.sub.3    C(CH.sub.3).sub.3                                                                         ##STR236##                                              CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR237##                                              CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR238##                                              CH.sub.3    CH.sub.2 CH(CH.sub.3).sub.2                                                               ##STR239##                                              N(CH.sub.3).sub.2                                                                          N(CH.sub.3).sub.2                                                                         ##STR240##                                              __________________________________________________________________________

If, for example, 2,6-difluorophenyl isocyanate and 5-ethyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one are used as starting substances, the course of the reaction in process (a) according to the invention can be outlined by the following equation: ##STR241## If, for example, 2-methylthio-benzenesulphonamide and 2-chlorocarbonyl-4-dimethylamino-2,4-dihydro-3H-1,2,4-triazol-3-one are used as starting substances, the course of the reaction in process (b) according to the invention can be outlined by the following equation: ##STR242## If, for example, N-methoxycarbonyl-2-methoxy-benzenesulphonamide and 5-diethylamino-4-difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one are used as starting substances, the course of the reaction in process (c) according to the invention can be outlined by the following equation: ##STR243## Formula (II) provides a general definition of the triazolinones to be used as starting substances in processes (a) and (c) according to the invention for the preparation of compounds of the formula (I).

In formula (II), R¹ and R² preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or particularly preferred, for R¹ and R².

Examples of the starting substances of the formula (II) are listed in Table 2 below. ##STR244##

                  TABLE 2                                                          ______________________________________                                         Examples of the starting substances of the                                     formula (II)                                                                   R.sup.1              R.sup.2                                                   ______________________________________                                         H                    H                                                         CH.sub.3             H                                                         C.sub.2 H.sub.5      H                                                         C.sub.3 H.sub.7      H                                                         CH(CH.sub.3).sub.2   H                                                         C.sub.4 H.sub.9      H                                                         CH.sub.2 CH(CH.sub.3).sub.2                                                                         H                                                         C(CH.sub.3).sub.3    H                                                         H                    CH.sub.3                                                  H                    C.sub.2 H.sub.5                                           H                    C.sub.3 H.sub.7                                           H                    CH(CH.sub.3).sub.2                                        H                    C.sub.4 H.sub.9                                           H                    CH.sub.2 CH(CH.sub.3).sub.2                               H                    C(CH.sub.3).sub.3                                         CHF.sub.2            H                                                         CH.sub.2 CH.sub.2 CN H                                                         CH.sub.2 CH.sub.2 OCH.sub.3                                                                         H                                                         H                    CF.sub.3                                                  H                    CH.sub.2 OCH.sub.3                                        H                    CH.sub.2 OC.sub.2 H.sub.5                                 H                    CH.sub.2 CH.sub.2 OCH.sub.3                               CH.sub.3             CH.sub.3                                                  CH.sub.3             C.sub.2 H.sub.5                                           CH.sub.3             C.sub.3 H.sub.7                                           CH.sub.3             CH(CH.sub.3).sub.2                                        CH.sub.3             C.sub.4 H.sub.9                                           CH.sub.3             CH.sub.2 CH(CH.sub.3).sub.2                               CH.sub.3             C(CH.sub.3).sub.3                                         C.sub.2 H.sub.5      CH.sub.3                                                  C.sub.3 H.sub.7      CH.sub.3                                                  CH(CH.sub.3).sub.2   CH.sub.3                                                  C.sub.4 H.sub.9      CH.sub.3                                                  CH.sub. 2 CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                  C.sub.2 H.sub.5      C.sub.2 H.sub.5                                           C.sub.3 H.sub.7      C.sub.3 H.sub.7                                           CHF.sub.2            C.sub.3 H.sub.7                                           CHF.sub.2            CH.sub.3                                                  CHF.sub.2            C.sub.2 H.sub.5                                           CH.sub.3             CF.sub.3                                                  C.sub.2 H.sub.5      CF.sub.3                                                  CF.sub.2 CHF.sub.2   CH.sub.3                                                  C.sub.2 H.sub.5      C.sub.3 H.sub.7                                           C.sub.2 H.sub.5      C.sub.4 H.sub.9                                           C.sub.6 H.sub.5      CH.sub.3                                                                       CH.sub.3                                                  CH.sub.3                                                                                             ##STR245##                                                ##STR246##          CH.sub.3                                                   ##STR247##          CH.sub.3                                                  CH.sub.3             N(CH.sub.3).sub.2                                         C.sub.2 H.sub.5      N(CH.sub.3).sub.2                                         C.sub.2 H.sub.5                                                                                      ##STR248##                                               C.sub.3 H.sub.7                                                                                      ##STR249##                                               OCH.sub.3                                                                                            ##STR250##                                                ##STR251##          C.sub.2 H.sub.5                                            ##STR252##          C.sub.3 H.sub.7                                            ##STR253##          CH.sub.3                                                   ##STR254##          C.sub.2 H.sub.5                                            ##STR255##          C.sub.3 H.sub.7                                            ##STR256##          C.sub.3 H.sub.7                                           CH.sub.3                                                                                             ##STR257##                                               CH.sub.3                                                                                             ##STR258##                                               NH.sub.2             CH.sub.3                                                  CH.sub.3             NHCH.sub.3                                                NHCH.sub.3           CH.sub.3                                                  NHCH.sub.3           C.sub.2 H.sub.5                                           NHCH.sub.3           C.sub.3 H.sub.7                                           N(CH.sub.3).sub.2    CH.sub.3                                                  N(CH.sub.3).sub.2    C.sub.2 H.sub.2                                           N(CH.sub.3).sub.2    C.sub.3 H.sub.7                                           OCH.sub.3            CH.sub.3                                                  OCH.sub.3            C.sub.2 H.sub.5                                           OC.sub.2 H.sub.5     CH.sub.3                                                  OC.sub.2 H.sub.5     C.sub.2 H.sub.5                                            ##STR259##                                                                                          ##STR260##                                                ##STR261##          CH.sub.2OC.sub.2 H.sub.5                                   ##STR262##          N(CH.sub.3).sub.2                                         O-C.sub.3 H.sub.7    C.sub.3 H.sub.7                                            ##STR263##                                                                                          ##STR264##                                                ##STR265##                                                                                          ##STR266##                                               OCH.sub.2CHCH.sub.2  CH.sub.3                                                  OCH.sub.2CHCH.sub.2  C.sub.2 H.sub.5                                           OCH.sub.2CHCH.sub.2  C.sub.3 H.sub.7                                            ##STR267##          C.sub.3 H.sub.7                                           OCH.sub.3                                                                                            ##STR268##                                               OCH.sub.3                                                                                            ##STR269##                                               OCH.sub.3                                                                                            ##STR270##                                               OCH.sub.3                                                                                            ##STR271##                                               OCH.sub.3                                                                                            ##STR272##                                               OCH.sub.3            N(CH.sub.3).sub.2                                         OCH.sub.2COOCH.sub.3 C.sub.3 H.sub.7                                           N(CH.sub.3).sub.2                                                                                    ##STR273##                                               N(CH.sub.3).sub.2                                                                                    ##STR274##                                               N(CH.sub.3).sub.2                                                                                    ##STR275##                                               OC.sub.2 H.sub.5     C.sub.3 H.sub.7                                           OC.sub.2 H.sub.5                                                                                     ##STR276##                                                ##STR277##                                                                                          ##STR278##                                                ##STR279##                                                                                          ##STR280##                                                ##STR281##          C.sub.2 H.sub.5                                           NHCH.sub.3           CH.sub.2OCH.sub.3                                          ##STR282##          CH.sub.2OCH.sub.3                                         CH.sub.3             CH.sub.2OCH.sub.3                                         ______________________________________                                    

The starting substances of the formula (II) are known and/or can be prepared by processes known per se (cf. Chem. Ber. 90 (1957), 909-921; loco. 98 (1965), 3025-3099; J. Heterocycl. Chem. 15 (1978), 237-240; Tetrahedron 32 (1976), 2347-2352; Helv. Chim. Acta 63 (1980), 841-859; J. Chem. Soc. C 1967, 746-751; EP-A 283,876; EP-A 294,666; EP-A 301,946; EP-A 298,371; DE-P 3,839,206/LEA 26,538 dated 19.11.1988; DE-P 3,916,207/LEA 26,849 dated 18.05.1989; DE-P 3,916,208/LEA 26,850 dated 18.05.1989; J. Chem. Soc. C 1970, 26-34; DE-P 3,916,930/LEA 26,886 dated 24.05.1989).

For example, the triazolinones of the formula (II) are obtained when

α) oxadiazolinones of the general formula (VII) ##STR283## in which R² has the abovementioned meaning are reacted with amino compounds of the general formula (VIII)

    H.sub.2 N--R.sup.1                                         (VIII)

in which

R¹ has the abovementioned meaning, at temperatures between 20° C. and 120° C. and, if appropriate, in the presence of a diluent, such as, for example, water, and the hydrazine derivatives formed by this process, of the general formula (IX) ##STR284## in which R¹ and R² have the abovementioned meanings, are isolated by customary methods (cf. the Preparation Examples) and--or if appropriate even without intermediate isolation--the compounds of the formula (IX) are condensed at temperatures between 20° C. and 120° C. and, if appropriate, in the presence of a basic condensation auxiliary, such as, for example, sodium hydroxide, and, if appropriate, in the presence of a diluent, such as, for example, water, to give the compounds of the formula (II) (cf. EP-A 301,946, DE-OS (German Published Specification) 3,743,493/LEA 25,759 and the Preparation Examples),

or when

β) amino compounds of the general formula (VIII)

    H.sub.2 N--R.sup.1                                         (VIII)

in which

R¹ has the abovementioned meaning, are reacted with carbonic acid derivatives, such as, for example, diphenyl carbonate, then with hydrazine or hydrazine hydrate and eventually with a carboxylic acid derivative or carbonic acid derivative of the general formula (X)

    (RO).sub.3 C--R.sup.2                                      (X)

in which

R² has the abovementioned meaning and

R represents lower alkyl, at temperatures between 0° C. and 150° C. and, if appropriate, in the presence of a diluent, such as, for example, ethylene chloride (cf. DE-P 3,920,270/LEA 26,937 dated 21.06.1989, DE-P 3,928,662/LEA 27,137 dated 30.08.1989, and the Preparation Examples).

The triazolinones of the general formula (IIa) ##STR285## in which A¹ represents in each case optionally substituted alkyl, alkenyl, cycloalkyl, alkoxy or dialkylamino and

A² represents hydrogen, or represents in each case optionally substituted alkyl, cycloalkyl, aralkyl aryl or alkoxy, provided that both A¹ and A² do not simultaneously represent alkyl,

are new and a subject of the present invention.

The new triazolinones of the formula (IIa) are obtained either when oxadiazolinones of the general formula (VIIa) ##STR286## in which A² has the abovementioned meaning, are reacted with amino compounds of the general formula (VIIIa)

    H.sub.2 N--A.sup.1                                         (VIIIa)

in which

A¹ has the abovementioned meaning, analogously to the process described above under (α), or when amino compounds of the general formula (VIIIa)

    H.sub.2 N--A.sup.1                                         (VIIIa)

are reacted with carbonic acid derivatives, then with hydrazine or hydrazinc hydrate and eventually with a carboxylic acid derivative or carbonic acid derivative of the general formula (Xa)

    (RO).sub.3 C--A.sup.2                                      (Xa)

in which

A² and R have the abovementioned meanings, analogously to the process described above under (β) (also see the Preparation Examples).

In the general formula (IIa),

A¹ preferably represents C₁ -C₆ -alkyl, C₃ -C₅ -alkenyl or C₃ -C₆ -cycloalkyl, or represents C₁ -C₆ -alkoxy which is optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxy-carbonyl, in particular methyl, ethyl, allyl, cyclopropyl, methoxy, ethoxy, propoxy or isopropoxy, or represents di-(C₁ -C₄ -alkyl)-amino, in particular dimethylamino or diethylamino, and

A² preferably represents hydrogen, or represents C₁ -C₆ -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C,-alkoxy, C₁ -C₄ -alkylcarbonyl or C₁ -C₄ -alkoxy-carbonyl, or represents C₃ -C₆ -cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or C₁ -C₄ -alkyl, or represents phenyl-C₁ -C₃ -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy and/or C₁ -C₄ -alkoxycarbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy, fluorine- and/or chlorine-substituted C₁ -C₃ -alkoxy, C₁ -C₄ -alkylthio, fluorine- and/or chlorine-substituted C₁ -C₃ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl and/or C₁ -C₄ -alkoxy-carbonyl, or represents C₁ -C₄ -alkoxy, in particular hydrogen, C₁ -C₄ -alkyl which is optionally substituted by fluorine and/or chlorine, methoxy or ethoxy, or represents C₃ -C₆ -cycloalkyl, or represents methoxy or ethoxy,

provided that both A¹ and A² do not simultaneously represent C₁ -C₆ -alkyl.

The compounds of the formulae (VII), (VIIa), (VIII), (VIIIa) and (X) or (Xa) which are to be used as starting substances for the preparation of the triazolinones of the formulae (II) or (IIa) are known (cf. Helv. Chim. Acta 55 (1972), 1174; EP-A 301,946; DE-OS (German Published Specification) 3,743,493).

Formula (III) provides a general definition of the sulphonyl isocyanates further to be used as starting substances in process (a) according to the invention for the preparation of compounds of the formula (I).

In formula (III), R³ preferably, or in particular, has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or particularly preferred, for R³.

Examples of the starting substances of the formula (III) which may be mentioned are: 2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-, 2-trifluoromethyl-, 2-difluoro-methoxy-, 2-trifluoromethoxy-, 2-methylthio-, 2-ethylthio-, 2-propylthio-, 2-methylsulphinyl-, 2-methylsulphonyl-, 2-dimethylaminosulphonyl-, 2-diethylaminosulphonyl-, 2-(N-methoxy-N-methyl)-aminosulphonyl-, 2-phenyl-, 2-phenoxy-, 2-methoxycarbonyl-, 2-ethoxycarbonyl-, 2-propoxycarbonyl- and 2-isopropoxycarbonyl-phenylsulphonyl isocyanate, 2-fluoro-, 2-chloro-, 2-difluoromethoxy-, 2-trifluorometh- 2-methoxycarbonyl- and 2-ethoxycarbonyl-benzylsulphonyl isocyanate, 2-methoxycarbonyl-3-thienyl-sulphonyl isocyanate, 4-methoxycarbonyl- and 4-ethoxycarbonyl-1-methylpyrazol-5-yl-sulphonyl isocyanate.

The sulphonyl isocyanates of the formula (III) are known and/or can be prepared by processes known per se (cf. U.S. Pat. Nos. 4,127,405, 4,169,719, 4,371,391; EP-A 7,687, 13,480, 21,641, 23,141, 23,422, 30,139, 35,893, 44,808, 44,809, 48,143, 51,466, 64,322, 70,041, 173,312).

Process (a) according to the invention for the preparation of the new compounds of the formula (I) is preferably carried out using diluents. Suitable diluents in this context are virtually all inert organic solvents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers, such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones, such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, esters, such as methyl acetate and ethyl acetate, nitriles, such as, for example, acetonitrile and propionitrile, amides, such as, for example, dimethylformamide, dimethylacetamide and N-methyl-pyrrolidone, and also dimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphoric triamide.

In process (a) according to the invention, the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temperatures between 0° C. and 150° C., preferably at temperatures between 10° C. and 80° C.

Process (a) according to the invention is generally carried out under atmospheric pressure.

For carrying out process (a) according to the invention, between 1 and 3 moles, preferably between 1 and 2 moles, of sulphonyl isocyanate of the formula (III) are generally employed per mole of triazolinone of the formula (II).

The reactants can be combined in any desired sequence. The reaction mixture is stirred until the reaction is complete and concentrated, and the crude product which remains in the residue is crystallized using a suitable solvent, such as, for example, diethyl ether. The product of the formula (I) which has been obtained in crystalline form is isolated by filtration with suction.

Formula (IV) provides a general definition of the triazolinone derivatives to be used as starting substances in process (b) according to the invention for the preparation of compounds of the formula (I).

In formula (IV), R¹ and R², preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or particularly preferred, for R¹ and R², and

Z preferably represents chlorine, C₁ -C₄ -alkoxy, benzyloxy or phenoxy, in particular methoxy or phenoxy.

Examples of the starting substances of the formula (IV) which are possible are the compounds of the formula (IV) to be prepared from the compounds of the formula (II) listed in Table 2 and phosgene, methyl chloroformate, benzyl chloroformate, phenyl chloroformate or diphenyl carbonate.

The starting substances of the formula (IV) are known and/or can be prepared by processes known per se (cf. EP-A 283,876; EP-A 294,666; EP-A 298,371.

The triazolinone derivatives of the formula (IV) are obtained for example when triazolinones of the general formula (II) ##STR287## in which R¹ and R² have the abovementioned meanings, are reacted with carbonic acid derivatives of the general formula (XI)

    Z--CO--Z.sup.1                                             (XI)

in which

Z has the abovementioned meaning and

Z¹ represents a leaving group, such as chlorine, methoxy, benzyloxy or phenoxy,

at temperatures between -20° C. and +100° C., if appropriate in the presence of a diluent, such as, for example, tetrahydrofuran, and, if appropriate, in the presence of an acid acceptor, such as, for example, sodium hydride or potassium tert-butylate (cf. the Preparation Examples).

Formula (V) provides a general definition of the sulphonamides further to be used as starting substances in process (b) according to the invention for the preparation of compounds of the formula (I).

In formula (V), R³ preferably, or in particular, has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or particularly preferred, for R³.

Examples of the starting substances of the formula (V) which may be mentioned are: 2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-, 2-trifluoromethyl-, 2-difluoro-methoxy-, 2-trifluoromethoxy-, 2-methylthio-, 2-ethylthio-, 2-propylthio-, 2-methylsulphinyl-, 2-methylsulphonyl-, 2-dimethylaminosulphonyl-, 2-diethylaminosulphonyl-, 2-(N-methoxy-N-methyl)-aminosulphonyl-, 2-phenyl-, 2-phenoxy-, 2-methoxycarbonyl-, 2-ethoxycarbonyl-, 2-propoxycarbonyl- and 2-isopropoxycarbonyl-benzenesulphonamide, 2-fluoro-, 2-chloro-, 2-difluoromethoxy-, 2-trifluoromethoxy-, 2-methoxycarbonyl- and 2-ethoxycarbonyl-phenylmethanesulphonamide, 2-methoxycarbonyl-3-thiophenesulphonamide, 4-methoxycarbonyl- and 4-ethoxycarbonyl-1-methyl-pyrazol- 5-sulphonamide.

The sulphonamides of the formula (V) are known and/or can be prepared by processes known per se (cf. U.S. Pat. Nos. 4,127,405, 4,169,719, 4,371,3917 EP-A 7,687, 13,480, 21,641, 23,141, 23,422, 30,422, 30,139, 35,893, 44,808, 44,809, 48,143, 51,466, 64,322, 70,041, 173,312).

Process (b) according to the invention for the preparation of the new compounds of the formula (I) is preferably carried out using diluents. Suitable diluents in this context are virtually all inert organic solvents, for example those which have been indicated above in the case of process (a) according to the invention.

Acid acceptors which can be employed in process (b) according to the invention are all acid-binding agents which can customarily be used for reactions of this type. The following are preferably suitable: alkali metal hydroxides, such as, for example, sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides, such as, for example, calcium hydroxide, alkali metal carbonates and alkali metal alcoholates, such as sodium carbonate, potassium carbonate, sodium tert-butylate and potassium tert-butylate, furthermore aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine, pyridine, 1,5-diazabicyclo-[4,3,0]-non-5-ene (DBN), 1,8-diazabicyclo-[5,4,0]-undec-7-ene (DBU) and 1,4-diazabicyclo-[2,2,2]-octane (DABCO).

When carrying out process (b) according to the invention, the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temperatures between 0° C. and 100° C., preferably at temperatures between 10° C. and 60° C.

In general, process (b) according to the invention is carried out under atmospheric pressure. However, it is also possible to carry out the process under increased or reduced pressure.

For carrying out process (b) according to the invention, the specifically required starting substances are generally employed in approximately equimolar amounts. However, it is also possible to use one of the two specifically employed components in a substantial excess. In general, the reactions are carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the specifically required temperature. Working-up in process (b) according to the invention is carried out in each case by customary methods.

The triazolinones of the formula (II) which are to be used as starting substances in process (c) according to the invention for the preparation of compounds of the formula (I) have already been described as starting substances for process (a) according to the invention.

Formula (VI) provides a general definition of the sulphonamide derivatives further to be used as starting substances in process (c) according to the invention for the preparation of compounds of the formula (I).

In formula (VI), R³ and Z preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) or (IV) according to the invention as being preferred, or particularly preferred, for R³ and Z.

Process (c) according to the invention is preferably carried out using diluents. Suitable diluents in this context are the same organic solvents as have been mentioned above in connection with the description of process (a) according to the invention.

If appropriate, process (c) is carried out in the presence of an acid acceptor. Suitable acid-binding agents in this context are the same as have been mentioned above in connection with the description of process (b) according to the invention.

When carrying out process (c) according to the invention the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temperatures between 0° C. and 100° C., preferably at temperatures between 10° C. and 60° C.

In general, process (c) according to the invention is carried out under atmospheric pressure. However, it is also possible to carry out the process under increased or reduced pressure.

For carrying out process (c) according to the invention, the specifically required starting substances are generally employed in approximately equimolar amounts. However, it is also possible to use one of the two specifically employed components in a substantial excess. In general, the reactions are carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the specifically required temperature. Working-up in process (c) according to the invention is carried out in each case by customary methods.

To convert the compounds of the formula (I) into salts, they are stirred with suitable salt formers, such as, for example, sodium hydroxide, sodium methylate, sodium ethylate, potassium hydroxide, potassium methylate or potassium ethylate, ammonia, isopropylamine, dibutylamine or triethylamine, using suitable diluents, such as, for example, water, methanol or ethanol. The salts can be isolated as crystalline products--then if appropriate after concentrating the mixture.

The active compounds according to the invention can be used as defoliants, desiccants, agents for destroying broad-leaved plants and, especially, as weedkillers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, for example, in connection with the following plants:

Dicotyledon weeds of the genera:

Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledon cultures of the genera:

Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the genera:

Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Arena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledon cultures of the genera:

Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.

However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.

The compounds are suitable, depending on the concentration, for the total combating of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for combating weeds in perennial cultures, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, in lawns, turf, meadows and pastures, and for the selective combating of weeds in annual cultures.

The compounds of the formula (I) according to the invention are suitable for combating monocotyledon and dicotyledon weeds both in the pre-emergence and the post-emergence method. They are markedly more effective than, for example, isocarbamide.

To a certain extent, the compounds according to the invention also show a fungicidal action, for example against powdery mildews and against apple scab, and also against Pyricularia oryzae on rice.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-forming agents.

In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. As liquid solvents, there are suitable in the main: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water.

As solid carriers there are suitable: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and silicates, as solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; as emulsifying and/or foam-forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well as albumen hydrolysis products; as dispersing agents there are suitable: for example lignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

For combating weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.

Suitable herbicides for the mixtures are known herbicides, such as, for example, 1-amino-6-ethylthio-3-(2,2-dimethylpropyl)-1,3,5-triazine-2,4(1H, 3H)-dione (AMETHYDIONE) or N-(2-benzothiazolyl)-N,N'-dimethylurea (METABENZTHIAZURON) for combating weeds in cereals; 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one (METAMITRON) for combating weeds in sugar beet and 4-amino-6-(1,1-dimethylethyl)-3-methylthio-1,2,4-triazin-5(4H)-one (METRIBUZIN) for combating weeds in soya beans; furthermore also mixtures with 2,4-dichlorophenoxyacetic acid (2,4-D); 4-(2,4-dichlorophenoxy)-butric acid (2,4-DB); 2,4-dichlorophenoxypropionic acid (2,4-DP); 5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitrobenzoic acid (ACIFLUORFEN); 2-chloro-2',6'-diethyl-N-methoxy-methylacetanilide (ALACHLOR); 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine (ATRAZINE); methyl 2-[[[[[(4,6-dimethoxypyrimidin-2-yl)-amino]carbonyl]amino]-sulphonyl]-methyl]-benzoate (BENSULFURON); 3-isopropyl-2,1,3-benzothiadiazin-4-one 2,2-dioxide (BENTAZONE); methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate (BIFENOX); 3,5-dibromo-4-hydroxy-benzonitrile; (BROMOXYNIL); N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)-acetamide (BUTACHLOR); ethyl 2-{[(4-chloro-6-methoxy-2-pyrimidinyl)-aminocarbonyl]-aminosulphonyl}benzoate(CHLORIMURON); 2-chloro-N-{[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl}-benzenesulphonamide (CHLORSULFURON); N,N-dimethyl-N'-(3-chloro-4-methylphenyl)-urea(CHLORTOLURON); 2-chloro-4-ethylamino-6-(3-cyanopropylamino)-1,3,5-triazine(CYANAZINE); 2,6-dichlorobenzonitrile (DICHLOBENIL); 2-[4-(2,4-dichlorophenoxy)phenoxy]-propionic acid, its methyl ester or its ethyl ester (DICLOFOP); 2-[(2-chlorophenyl)-methyl]-4,4-dimethylisoxazolidin-3-one (DIMETHAZONE); 4-amino-6-t-butyl-3-ethylthio-1,2,4-triazin-5(4H)-one (ETHIOZIN); 2-{4-[6-chloro-2-benzoxazolyl)-oxy]-phenoxy}-propanoic acid, its methyl ester or its ethyl ester (FENOXAPROP); 2-[4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy]-propanoic acid or its butyl ester (FLUAZIFOP); N,N-dimethyl-N'-(3 -trifluoromethylphenyl)-urea (FLUOMETURON); 1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)-4-pyridone (FLURIDONE); 5-(2-chloro-4-trifluoromethyl-phenoxy)-N-methylsulphonyl-2-nitrobenzamide (FOMESAFEN); N-phosphonomethyl-glycine (GLYPHOSATE); methyl 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo- 1H-imidazol-2-yl]-4(5)-methylbenzoate (IMAZAMETHABENZ); 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-pyridine-3-carboxylic acid (IMAZAPYR); 2-[5-methyl-5-(1-methylethyl)-4-oxo-2-imidazolin-2-yl]-3-quinolincarboxylic acid (IMAZAQUIN); 2-[4,5-dihydro-4-methyl-4-isopropyl-5-oxo-(1H)-imidazol-2-yl]-5-ethylpyridin-3-carboxylic acid (IMAZETHAPYR); 3,5-diiodo-4-hydroxybenzonitrile (IOXYNIL); N,N-dimethyl-N'-(4-isopropylphenyl)-urea (ISOPROTURON); (2-methyl-4-chlorophenoxy)-acetic acid (MCPA); (4-chloro-2-methylphenoxy)propionic acid (MCPP); N-methyl-2-(1,3-benzothiazol-2-yloxy)-acetanilide (MEFENACET); 2-chloro-N-(2,6-dimethylphenyl)-N-[(1H)-pyrazol-1-yl-methyl]-acetamide (METAZACHLOR); 2-ethyl-6-methyl-N-(1-methyl-2-methoxyethyl)-chloroacetanilide (METOLACHLOR); 2-{[[((4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino)-carbonyl]amino]-sulphonyl}-benzoic aicd or its methyl ester (METSULFURON); 1-(3-trifluoromethyl-phenyl)-4-methylamino-5-chloro-6-pyridazone (NORFLURAZON); N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitroaniline (PENDIMETHALIN); 0-(6-chloro-3-phenyl-pyridazin-4-yl) S-octyl thiocarbamate (PYRIDATE); ethyl 2-[4-(6-chloro-quinoxalin-2-yl-oxy)-phenoxy]-propionate (QUIZALOFOP-ETHYL); 2-[ 1-(ethoxamino)-butylidene]-5-(2-ethylthiopropyl)-1,3cyclohexadione (SETHOXYDIM); methyl 2-{[(4,6-dimethyl-2-pyrimidinyl)-aminocarbonyl]-aminosulphonyl}-benzoate (SULFOMETURON); 4-ethylamino-2-t-butylamino-6-methylthio-s-triazine (TERBUTRYNE); methyl 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl]-amino]-sulphonyl]-thiophene-2-carboxylate (THIAMETURON); S-( 2,3,3-trichloroallyl)-N,N-diisopropylthiocarbamate (TRI-ALLATE), 2,6-dinitro-4-trifluoromethyl-N,N-dipropylaniline (TRIFLURALIN). Suprisingly, some mixtures also show a synergistic effect.

Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied either before or after emergence of the plants.

They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 0.01 and 15 kg of active compound per hectare of soil surface, preferably between 0.05 and 10 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the following examples.

PREPARATION EXAMPLES Example 1 ##STR288##

(Process (a))

3.0 g (17.95mmol) of 4-cyclopentyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one are dissolved in 60 ml of acetonitrile, and 6.9 g (28.6 mmol) of 2-methoxycarbonylphenylsulphonyl isocyanate, dissolved in 20 ml of acetonitrile, are added to this solution with stirring. The reaction mixture is stirred for 6 hours at 20° C. and then concentrated. The residue which remains is stirred with diethyl ether, and the product which has been obtained in crystalline form is isolated by filtration with suction.

This gives 6.6 g (90% of theory) of 4-cyclopentyl-5-methyl-2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 146° C.

Example 2 ##STR289##

(Process (b))

1,8 g (11.8 mmol) of 1,8-diazabicyclo-[5,4,0]-undec-7-ene (DBU) are added to a stirred mixture of 3.0 g (12.1 mmol) of 5-ethyl-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2.5 g (12.2 mmol) of 2-chloro-6-methyl-benzenesulphonamide and 60 ml of acetonitrile. The reaction mixture is stirred for 2 hours at 20° C., then poured into about twice the volume of ice-water, and a pH of about 2 is established by dropwise addition of concentrated hydrochloric acid. The product which has been obtained during this process in crystalline form is isolated by filtration with suction.

This gives 3.2 g (73.5% of theory) of 5-ethyl-4-methyl-2-(2-chloro-6-methyl-phenylsulphonyl-aminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 176° C.

For example the compounds of the formula (I) listed in Table 3 below can also be prepared analogously to Examples 1 and 2 and following the general instructions of the preparation processes according to the invention. ##STR290##

                                      TABLE 3                                      __________________________________________________________________________     Preparation Examples of the compounds of the formula (1) (m.p. = melting       point):                                                                        Ex. No.                                                                             R.sup.1     R.sup.2   R.sup.3       m.p. (°C.)                     __________________________________________________________________________     3    C.sub.6 H.sub.5                                                                            CH.sub.3                                                                                               158                                   4    CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR291##   159                                   5    C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                           ##STR292##   115                                   6    CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR293##   143                                   7    C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                           ##STR294##   139                                   8    CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR295##   141                                   9    OCH.sub.3   CH.sub.3                                                                                  ##STR296##   121                                   10   OCH.sub.3   CH.sub. 3                                                                                 ##STR297##   180                                   11   OCH.sub.3   CH.sub.3                                                                                  ##STR298##   149                                   12   OCH.sub.3   C.sub.2 H.sub.5                                                                           ##STR299##   144                                   13   OCH.sub.3   C.sub.3 H.sub.7                                                                           ##STR300##   128                                   14   CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR301##   173                                   15   CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR302##   133                                   16                                                                                   ##STR303## C.sub.2 H.sub.5                                                                           ##STR304##   154                                   17   OCH.sub.3   CH(CH.sub.3).sub.2                                                                        ##STR305##   137                                   18                                                                                   ##STR306## C.sub.2 H.sub.5                                                                           ##STR307##   174                                   19                                                                                   ##STR308## C.sub.3 H.sub.7                                                                           ##STR309##    97                                   20   CH.sub.3    N(CH.sub.3).sub.2                                                                         ##STR310##   168                                   21   OCH.sub.2 C.sub.6 H.sub.5                                                                  CH.sub.3                                                                                  ##STR311##   174                                   22   C.sub.2 H.sub.5                                                                            C.sub.3 H.sub.7                                                                           ##STR312##   136                                   23   N(CH.sub.3).sub.2                                                                          C.sub.2 H.sub.5                                                                           ##STR313##   139                                   24   N(CH.sub.3).sub.2                                                                          H                                                                                         ##STR314##   197                                   25   N(CH.sub.3).sub.2                                                                          CH(CH.sub.3).sub.2                                                                        ##STR315##   148                                   26   OC.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                           ##STR316##   153                                   27   OC.sub.2 H.sub.5                                                                           C.sub.3 H.sub.7                                                                           ##STR317##   155                                   28                                                                                   ##STR318## CH(CH.sub.3).sub.2                                                                        ##STR319##   186                                   29                                                                                   ##STR320## C.sub.3 H.sub.7                                                                           ##STR321##   146                                   30   N(CH.sub.3).sub.2                                                                          C.sub.3 H.sub.7                                                                           ##STR322##   110                                   31   N(CH.sub.3).sub.2                                                                           ##STR323##                                                                               ##STR324##   131                                   32   C.sub.2 H.sub.5                                                                            C.sub.4 H.sub.9                                                                           ##STR325##   98                                    33   CH.sub.3    C.sub.4 H.sub.9                                                                           ##STR326##   113                                   34   C.sub.3 H.sub.7                                                                            C.sub.4 H.sub.9                                                                           ##STR327##   88                                    35                                                                                   ##STR328## C.sub.4 H.sub.9                                                                           ##STR329##   117                                   36   OCH.sub.3   C.sub.4 H.sub.9                                                                           ##STR330##   117                                   37   CH.sub.3                                                                                    ##STR331##                                                                               ##STR332##   141                                   38   C.sub.2 H.sub.5                                                                             ##STR333##                                                                               ##STR334##   130                                   39   C.sub.3 H.sub.7                                                                             ##STR335##                                                                               ##STR336##   139                                   40                                                                                   ##STR337##                                                                                 ##STR338##                                                                               ##STR339##   151                                   41                                                                                   ##STR340## CH.sub.3                                                                                  ##STR341##   151                                   42   CH(CH.sub.3).sub.2                                                                         NHCH(CH.sub.3).sub.2                                                                      ##STR342##   135                                   43   N(CH.sub.3).sub.2                                                                          N(CH.sub.3).sub.2                                                                         ##STR343##   171                                   44   CH.sub.3    C.sub.3 H.sub.7                                                                           ##STR344##   168                                   45   C.sub.2 H.sub.5                                                                            N(CH.sub.3).sub.2                                                                         ##STR345##   134                                   46   CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR346##   167                                   47   NH.sub. 2   C.sub.3 H.sub.7                                                                           ##STR347##   120                                   48                                                                                   ##STR348##                                                                                 ##STR349##                                                                               ##STR350##   120                                   49                                                                                   ##STR351## H                                                                                         ##STR352##   195                                   50   CH.sub.2 CHCH.sub.2                                                                        C.sub.2 H.sub.5                                                                           ##STR353##   108                                   51   CH.sub.2 CHCH.sub.2                                                                        H                                                                                         ##STR354##   158                                   52   OCH.sub.3   C.sub.3 H.sub.7                                                                           ##STR355##   110-111                               53                                                                                   ##STR356## H                                                                                         ##STR357##   212-214                               54   C.sub.3 H.sub.7                                                                            H                                                                                         ##STR358##   168-169                               55                                                                                   ##STR359## C.sub.3 H.sub.7                                                                           ##STR360##   103- 105                              56                                                                                   ##STR361## C.sub.2 H.sub.5                                                                           ##STR362##   127                                   57   OCH.sub.3   C.sub.2l H.sub.5                                                                          ##STR363##   111-113                               58   OCH.sub.3                                                                                   ##STR364##                                                                               ##STR365##   139                                   59   NHCH.sub.3  C.sub.3 H.sub.7 -n                                                                        ##STR366##   196                                   60   CH.sub.3    C.sub.3 H.sub.7 -n                                                                        ##STR367##   178                                   61                                                                                   ##STR368## H                                                                                         ##STR369##   177                                   62   CH.sub.2 CH(CH.sub.3).sub.2                                                                C.sub.2 H.sub.5                                                                           ##STR370##   123                                   63   CH.sub.2CHCH.sub.2                                                                         C.sub.3 H.sub.7 -n                                                                        ##STR371##   (amorphous)                           64                                                                                   ##STR372## C.sub.2 H.sub.5                                                                           ##STR373##   157                                   65                                                                                   ##STR374## C.sub.2 H.sub.5                                                                           ##STR375##   117                                   66   C(CH.sub.3).sub.3                                                                          C.sub.2 H.sub.5                                                                           ##STR376##   182                                   67                                                                                   ##STR377## C.sub.2 H.sub.5                                                                           ##STR378##   133                                   68                                                                                   ##STR379## C.sub.2 H.sub.5                                                                           ##STR380##   162                                   69   CH.sub.2 CHCH.sub.2                                                                        CH.sub.3                                                                                  ##STR381##   120                                   70                                                                                   ##STR382## C.sub.2 H.sub.5                                                                           ##STR383##   183                                   71   C.sub.2 H.sub.5                                                                            H                                                                                         ##STR384##   196                                   72                                                                                   ##STR385## CH.sub.3                                                                                  ##STR386##   153                                   73   OCH.sub.3                                                                                   ##STR387##                                                                               ##STR388##   138                                   74   CH(CH.sub.3).sub.2                                                                         H                                                                                         ##STR389##   191                                   75                                                                                   ##STR390## H                                                                                         ##STR391##   191                                   76                                                                                   ##STR392## H                                                                                         ##STR393##   192                                   77   C(CH.sub.3).sub.3                                                                          H                                                                                         ##STR394##   211                                   78                                                                                   ##STR395## CH.sub.3                                                                                  ##STR396##   110                                   79   CH.sub.3    CH.sub.2 OCH.sub.3                                                                        ##STR397##   152                                   80   CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR398##   174                                   81   CH.sub.3    CH.sub.2 OC.sub.2 H.sub.5                                                                 ##STR399##   123                                   82   OCH.sub.3   C.sub.3 H.sub.7 -n                                                                        ##STR400##   (amorphous)                           83                                                                                   ##STR401## C.sub.2 H.sub.5                                                                           ##STR402##   124                                   84                                                                                   ##STR403## CH.sub.2 OCH.sub.3                                                                        ##STR404##   102                                   85                                                                                   ##STR405## CH.sub.2 OCH.sub.3                                                                        ##STR406##   155                                   86                                                                                   ##STR407## CH.sub.2 OC.sub.2 H.sub.5                                                                 ##STR408##   123                                   87                                                                                   ##STR409## CH.sub.2 OC.sub.2 H.sub.5                                                                 ##STR410##    99                                   88                                                                                   ##STR411## N(CH.sub.3).sub.2                                                                         ##STR412##   189                                   89   OCH.sub.3   C.sub.2 H.sub.5                                                                           ##STR413##   155                                   90                                                                                   ##STR414## C.sub.2 H.sub.5                                                                           ##STR415##   133                                   91   OCH.sub.3   C.sub.3 H.sub.7 -n                                                                        ##STR416##   125                                   92                                                                                   ##STR417## C.sub.2 H.sub.5                                                                           ##STR418##   138                                   93   OCH.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                           ##STR419##   132                                   94   OCH.sub.2 H.sub.5                                                                          C.sub.3 H.sub.7 -n                                                                        ##STR420##   107                                   95   OCH.sub.3   CH(CH.sub.3).sub.2                                                                        ##STR421##   128                                   96   OCH.sub.3   CH.sub.3                                                                                  ##STR422##   119                                   97                                                                                   ##STR423## C.sub.3 H.sub.7 -n                                                                        ##STR424##   100                                   98                                                                                   ##STR425##                                                                                 ##STR426##                                                                               ##STR427##   140                                   99                                                                                   ##STR428## N(CH.sub.3).sub.2                                                                         ##STR429##   163                                   100                                                                                  ##STR430## N(CH.sub.3).sub.2                                                                         ##STR431##   182                                   101  CH.sub.3    N(CH.sub.3).sub.2                                                                         ##STR432##   181                                   102  CH.sub.3    OCH.sub.3                                                                                 ##STR433##   150                                   103  C.sub.2 H.sub.5                                                                             ##STR434##                                                                               ##STR435##   147                                   104  CH.sub.2CHCH.sub.2                                                                         CH.sub.3                                                                                  ##STR436##   132                                   105  CH.sub.2CHC.sub.2 H.sub.5                                                                  CH.sub.3                                                                                  ##STR437##   109                                   106  CH.sub.2CHCH.sub.2                                                                         C.sub.3 H.sub.7 -n                                                                        ##STR438##   104                                   107  OC.sub.2 H.sub.7                                                                           C.sub.2 H.sub.5                                                                           ##STR439##   147                                   108  OC.sub.2 H.sub.7                                                                           C.sub.3 H.sub.7 -n                                                                        ##STR440##   136                                   109  OCH.sub.3   CH(CH.sub.3).sub.2                                                                        ##STR441##   126                                   110  CH.sub.3    CH.sub.3                                                                                  ##STR442##   146                                   111                                                                                  ##STR443## CH.sub.3                                                                                  ##STR444##   175                                   112  CH.sub.3    CH(CH.sub.3).sub.2                                                                        ##STR445##   124                                   113  CH.sub.3                                                                                    ##STR446##                                                                               ##STR447##   171                                   114                                                                                  ##STR448## CH(CH.sub.3).sub.2                                                                        ##STR449##   132                                   115                                                                                  ##STR450##                                                                                 ##STR451##                                                                               ##STR452##   167                                   116  CH.sub.3    CH.sub.3                                                                                  ##STR453##   155                                   117  CH.sub.3    C.sub.2 H.sub.5                                                                           ##STR454##   147                                   118  CH.sub.3    C.sub.3 H.sub.7 -n                                                                        ##STR455##   169                                   119  OCH.sub.3   C.sub.2 H.sub.5                                                                           ##STR456##                                         120                                                                                  ##STR457## C.sub.2 H.sub.5                                                                           ##STR458##   132                                   __________________________________________________________________________

Example 121 ##STR459##

A mixture of 3.8 g (0.03 mol) of 5-ethyl-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 12 g (0.05 mol) of 2-methoxy-carbonyl-phenylsulphonyl isocyanate and 50 ml of methylene chloride is stirred at 20° C. for 20 hours and then evaporated under a waterpump vacuum. The residue is triturated with diethyl ether, and the crystalline product which is obtained during this process is isolated by filtering off with suction.

6 g (54% of theory) of 5-ethyl-4-methyl-2-(2-methoxycarbonyl-phenylsulphonyl-aminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 131° C. are obtained.

In analogy to Example 121 and following the general description of the preparation process according to the invention, for example the compounds of the formula (1) which are listed in Table 3 below can be prepared. ##STR460##

                                      TABLE 3                                      __________________________________________________________________________     continuation                                                                   Ex. No.                                                                             R.sup.1   R.sup.2 R.sup.3   m.p. (°C.)                             __________________________________________________________________________     122  C.sub.2 H.sub.5                                                                          H                                                                                                118                                           123  CH.sub.3  CH.sub.3                                                                                ##STR461##                                                                              172                                           124  CH.sub.3  C.sub.2 H.sub.5                                                                         ##STR462##                                                                              122                                           125  CH.sub.3  CH.sub.2 CH.sub.2 OCH.sub.3                                                             ##STR463##                                                                              amorphous                                     126  CH.sub.3  C.sub.2 H.sub.5                                                                         ##STR464##                                                                              164                                           127  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                         ##STR465##                                                                              172                                           128  CH.sub.3  C.sub.3 H.sub.7 -n                                                                      ##STR466##                                                                              132                                           129  C.sub.2 H.sub.5                                                                          C.sub.3 H.sub.7 -n                                                                      ##STR467##                                                                              153                                           130  CH(CH.sub.3).sub.2                                                                       C.sub.3 H.sub.7 -n                                                                      ##STR468##                                                                              157                                           131  CH.sub.3  C.sub.2 H.sub.5                                                                         ##STR469##                                                                              200                                           132  C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                ##STR470##                                                                              173                                           133  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                         ##STR471##                                                                              207                                           134  CH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                ##STR472##                                                                              127                                           135  CH(CH.sub.3).sub.2                                                                       CH(CH.sub.3).sub.2                                                                      ##STR473##                                                                              142                                           136  CH(CH.sub.3).sub.2                                                                       C.sub.2 H.sub.5                                                                         ##STR474##                                                                              112                                           137  CH.sub.3  CH(CH.sub.3).sub.2                                                                      ##STR475##                                                                              125                                           138  C.sub.2 H.sub.5                                                                          CH(CH.sub.3).sub.2                                                                      ##STR476##                                                                              250                                           139  C.sub.3 H.sub.7 -n                                                                       CH(CH.sub.3).sub.2                                                                      ##STR477##                                                                              255                                           140  CH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                ##STR478##                                                                              165                                           141  C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                ##STR479##                                                                              180                                           142  C.sub.3 H.sub.7 -n                                                                       C.sub.2 H.sub.5                                                                         ##STR480##                                                                              187                                           143  CH(CH.sub.3).sub.2                                                                       C.sub.2 H.sub.5                                                                         ##STR481##                                                                              133                                           144  CH.sub.3  C.sub.3 H.sub.7 -n                                                                      ##STR482##                                                                              225                                           145  C.sub.2 H.sub.5                                                                          C.sub.3 H.sub.7 -n                                                                      ##STR483##                                                                              173                                           146  C.sub.3 H.sub.7 -n                                                                       C.sub.3 H.sub.7 -n                                                                      ##STR484##                                                                              143                                           147  CH(CH.sub.3).sub.2                                                                       C.sub.3 H.sub.7 -n                                                                      ##STR485##                                                                              120                                           148  CH.sub.3  CH(CH.sub.3).sub.2                                                                      ##STR486##                                                                              147                                           149  C.sub.2 H.sub.5                                                                          CH(CH.sub.3).sub.2                                                                      ##STR487##                                                                              187                                           150  C.sub.3 H.sub.7 -n                                                                       CH(CH.sub.3).sub.2                                                                      ##STR488##                                                                               78                                           151  CH(CH.sub.3).sub.2                                                                       CH(CH.sub.3).sub.2                                                                      ##STR489##                                                                              167                                           152  CH.sub.3  C.sub.2 H.sub.5                                                                         ##STR490##                                                                              144                                           153  CH.sub.3  CH.sub.3                                                                                ##STR491##                                                                              133                                           154  C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                ##STR492##                                                                              141                                           155                                                                                  ##STR493##                                                                              CH.sub.3                                                                                ##STR494##                                                                              144                                           156                                                                                  ##STR495##                                                                              CH.sub.3                                                                                ##STR496##                                                                              173                                           157  N(CH.sub.3).sub.2                                                                        CH.sub.3                                                                                ##STR497##                                                                              165                                           __________________________________________________________________________

STARTING SUBSTANCES OF THE FORMULA (II) Example (II-1) ##STR498## Step 1 ##STR499##

A mixture of 68.5 g (0.60 mol) of 5-methyl-1,3,4-oxadiazolin-2-one, 45.8 g (0.75 mol) of 0-ethyl-hydroxylamine and 400 ml of water is refluxed for 12 hours and then concentrated. The residue is taken up in ethanol and reconcentrated. The residue which is obtained in this process is stirred with diethyl ether, and the product which has been obtained in crystalline form is isolated by filtration with suction.

This gives 77.5 g (74% of theory) of 1-ethoxyaminocarbonyl-2-propionyl-hydrazine of melting point 122° C.

Step 2 ##STR500##

A mixture of 75.5 g (0.43 mol) of 1-ethoxyaminocarbonyl-2-propionyl-hydrazine, 17.5 g (0.44 mol) of sodium hydroxide and 300 ml of water is refluxed for 12 hours. When the mixture is cold, a ph of between 3 and 4 is established by adding concentrated hydrochloric acid, and the mixture is concentrated. The residue is stirred with ethyl acetate, and the sodium chloride which has remained undissolved is separated off by filtration with suction. The filtrate is concentrated, the residue is stirred with diethyl ether, and the product which has been obtained in crystalline form is isolated by filtration with suction.

This gives 37 g (55% of theory) of 4-ethoxy-5-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 93° C.

Example (II-2) ##STR501##

A mixture of 40 g (0.31 mol) of 5-propyl-1,3,4-oxadiazolin- 2-one, 109 g of aqueous methylamine solution (32% strength, 1.125 mol of CH₃ NH₂) and 500 ml of water is refluxed for 12 hours and then concentrated. The residue is taken up in ethanol and reconcentrated. The residue obtained in this process is stirred with diethyl ether, and the product which has been obtained in crystalline form is isolated by filtration with suction.

This gives 31.7 g (72% of theory) of 4-methyl-5-propyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 86° C.

Example (II-3) ##STR502##

856 g (4.0 mol) of diphenyl carbonate are dissolved in 588 g of ethylene chloride. 245 g (4.0 mol) of dimethylhydrazine (98% pure) are added dropwise with water-cooling, and the mixture is heated slowly and, for 4 hours, stirred at 60° C.

After the mixture has cooled to 20° C., 200 g (4.0 mol) of hydrazine hydrate are added dropwise, and the mixture is then stirred for 12 hours. It is warmed to 70°-80° C. and, for about 1 hour, stirring is continued. When cold, the solution is distilled in vacuo, during which process ethylene chloride and water are removed (final bottom temperature 100° C.). The above phenolic dimethyl carbodihydrazide solution is added dropwise in the course of 90 minutes at reflux temperature (about 102° C.) to 424 g (4.0 mol) of trimethyl orthoformate. After the methanol which has formed is removed by distillation, phenol is distilled off in vacuo, after which 282 g of product mixture are obtained at a head temperature of 85°-105° C. This mixture is boiled with 600 ml of acetone, and filtered at boiling point, and the filtrate is then cooled. The product which has been obtained in this process in crystalline form is isolated by filtration with suction.

This gives 71 g (14% of theory) of 4-dimethylamino-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 127° C.

For example the compounds of the formulae (II) and (IIa) listed in Table 4 below can also be prepared analogously to Examples (II-1) to (II-3). ##STR503##

                  TABLE 4                                                          ______________________________________                                         Preparation examples of the compounds of the                                   formula (II)                                                                   Ex.                                 m.p.                                       No.   R.sup.1          R.sup.2      (°C.)                               ______________________________________                                         II-4  C.sub.3 H.sub.7  CH.sub.3      48                                        II-5  CH(CH.sub.3).sub.2                                                                              CH.sub.3     118                                        II-6  CH.sub.3         CH.sub.3     139                                        II-7  C.sub.2 H.sub.5  C.sub.2 H.sub.5                                                                             117                                        II-8  C.sub.3 H.sub.7  C.sub.2 H.sub.5                                                                             42-45                                      II-9  CH(CH.sub.3).sub.2                                                                              C.sub.2 H.sub.5                                                                             102                                        II-10 C.sub.2 H.sub.5  C.sub.3 H.sub.7                                                                              97                                        II-11 C.sub.3 H.sub.7  C.sub.3 H.sub.7                                                                             (amor-                                                                         phous)                                     II-12 CH(CH.sub.3).sub.2                                                                              C.sub.3 H.sub.7                                                                              91                                        II-13 CH.sub.3         CH(CH.sub.3).sub.2                                                                           92                                        II-14 C.sub.2 H.sub.5  CH(CH.sub.3).sub.2                                                                          (amor-                                                                         phous)                                     II-15 C.sub.3 H.sub.7  CH(CH.sub.3).sub.2                                                                          (amor-                                                                         phous)                                     II-16 CH(CH.sub.3).sub.2                                                                              CH(CH.sub.3).sub.2                                                                          168                                        II-17 C.sub.2 H.sub.5  CH.sub.3     134                                        II-18                                                                                                 CH.sub.3     159                                        II-19 OCH.sub.3        CH.sub.3     178                                        II-20 OCH.sub.3        C.sub. 2 H.sub.5                                                                            140                                        II-21 OCH.sub.3        C.sub.3 H.sub.7                                                                             127                                        II-22 OCH.sub.3        CH(CH.sub.3).sub.2                                                                          130                                        II-23 OCH.sub.2 C.sub.6 H.sub.5                                                                       CH.sub.3     106                                        II-24                                                                                 ##STR504##      C.sub.2 H.sub.5                                                                             150                                        II-25                                                                                 ##STR505##      C.sub.3 H.sub.7                                                                             130                                        II-26 OC.sub.2 H.sub.5 C.sub.3 H.sub.7                                                                              72                                        II-27                                                                                 ##STR506##      CH(CH.sub.3).sub.2                                                                          121                                        II-28 CH.sub.3         C.sub.4 H.sub.9                                                                              50                                        II-29 C.sub.2 H.sub.5  C.sub.4 H.sub.9                                                                              76                                        II-30 C.sub.3 H.sub.7  C.sub.4 H.sub.9                                                                             (amor-                                                                         phous)                                     II-31 OCH.sub.3        C.sub.4 H.sub.9                                                                             100                                        II-32                                                                                 ##STR507##      C.sub.4 H.sub.9                                                                              66                                        II-33 CH.sub.3                                                                                         ##STR508##   68                                        II-34 C.sub.2 H.sub.5                                                                                  ##STR509##  130                                        II-35 C.sub.3 H.sub.7                                                                                  ##STR510##   68                                        II-36                                                                                 ##STR511##                                                                                      ##STR512##  154                                        II-37 N(CH.sub.3).sub.2                                                                               CH.sub.3     153                                        II-38 N(CH.sub.3).sub.2                                                                               C.sub.2 H.sub. 5                                                                            114                                        II-39 N(CH.sub.3).sub.2                                                                               C.sub.3 H.sub.7                                                                             108                                        II-40 N(CH.sub.3).sub.2                                                                               CH(CH.sub.3).sub.2                                                                          100                                        II-41 CH.sub.3         N(CH.sub.3).sub.2                                                                            80                                        II-42 N(CH.sub.3).sub.2                                                                                ##STR513##  134                                        II-43 CH(CH.sub.3).sub.2                                                                              NHCH(CH.sub.3).sub.2                                                                        205                                        II-44 N(CH.sub.3).sub.2                                                                               N(CH.sub.3).sub.2                                                                            93                                        II-45 C.sub.2 H.sub.5  N(CH.sub.3).sub.2                                                                            50                                        II-46                                                                                 ##STR514##      CH.sub.3     145                                        II-47                                                                                 ##STR515##      CH.sub.3     163                                        II-48                                                                                 ##STR516##      H            102                                        II-49 OCH.sub.3                                                                                        ##STR517##  136-137                                    II-50 CH.sub.3         C.sub.6 H.sub.5                                         II-51 NH.sub.2         H            192                                        II-52 NH.sub.2         CH.sub.3     230                                        II-53 NH.sub.2         CF.sub.3     163                                        II-54 NHCH.sub.3       CH(CH.sub.3).sub.2                                                                          105                                        II-55 NHCH.sub.3                                                                                       ##STR518##   95                                        II-56 NH.sub.2         C.sub.2 H.sub.5                                                                             170                                        II-57 NH.sub.2         C.sub.3 H.sub.7                                                                             147                                        II-58 NHCH.sub.3       NHCH.sub.3   137                                        II-59 CH.sub.2 C.sub.6 H.sub.5                                                                        C.sub.2 H.sub.5                                                                             125                                        II-60 NHCH.sub.3       H            133                                        II-61 NHCH.sub.3       N(CH.sub.3).sub.2                                                                           129                                        II-62 NHCH.sub.3       C.sub.3 H.sub.7                                                                              76                                        II-63 NH.sub.2                                                                                         ##STR519##  248                                        II-64 NH.sub.2                                                                                         ##STR520##  176                                        II-65 NH.sub.2                                                                                         ##STR521##  183                                        II-66 NH.sub.2                                                                                         ##STR522##  210                                        II-67 NHCH.sub.3       C.sub.2 H.sub.5                                                                             101                                        II-68 NH.sub.2         N(C.sub.2 H.sub.5).sub.2                                                                    196                                        II-69 NH.sub.2                                                                                         ##STR523##  233                                        II-70 NH.sub.2         CH(CH.sub.3).sub.2                                                                          172                                        II-71 NH.sub.2         C(CH.sub.3).sub.3                                                                           261                                        II-72 NH.sub.2         CH.sub.2 CH.sub.2 OCH.sub.3                                                                  98                                        II-73 NH.sub.2         C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                           213                                        II-74 NH.sub.2         NHC.sub.2 H.sub.5                                                                           220                                        II-75 NH.sub.2         OCH.sub.3    (amor-                                                                         phous)                                     II-76 NH.sub.2         CH.sub.2 OCH.sub.3                                                                          134                                        II-77 NH.sub.2         CH.sub.2 OC.sub.2 H.sub.5                                                                   104                                        II-78 N(CH.sub.3).sub.2                                                                               CH.sub.3     153                                        II-79                                                                                 ##STR524##      C.sub.2 H.sub.5                                                                             103                                        II-80 CH.sub.2 CH(CH.sub.3).sub.2                                                                     C.sub.2 H.sub.5                                                                             105                                        II-81 C.sub.6 H.sub.5  H            183                                        II-82 N(CH.sub.3).sub.2                                                                               CH(CH.sub.3).sub.2                                                                          (amor-                                                                         phous)                                     II-83 NHCH.sub.3       CH.sub.3     114                                        II-84 NH.sub.2         CH.sub.2 C.sub.6 H.sub.5                                                                    168                                        II-85 NH.sub.2         N(CH.sub.3).sub.2                                                                           207                                        II-86 NH.sub.2         C.sub.6 H.sub.5                                                                             230                                        II-87 NH.sub.2                                                                                         ##STR525##  223                                        II-88 NH.sub.2         NHCH(CH.sub.3).sub.2                                                                        152                                        II-89 NHCH.sub.3       NHCH(CH.sub.3).sub.2                                                                        120                                        II-90                                                                                 ##STR526##                                                                                      ##STR527##  254                                        II-91                                                                                 ##STR528##      N(CH.sub.3).sub.2                                       II-92 CH.sub.2 C.sub.6 H.sub.5                                                                        H            111                                        II-93 C.sub.3 H.sub.7  H             48                                        II-94 C.sub.6 H.sub.5  C.sub.2 H.sub.5                                                                             124                                        II-95 C(CH.sub.3).sub.3                                                                               C.sub.2 H.sub.5                                                                             158                                        II-96 CH.sub.3         H            157                                        II-97                                                                                 ##STR529##      C.sub.2 H.sub.5                                                                             108                                        II-98                                                                                 ##STR530##      C.sub.2 H.sub.5                                                                             132                                        II-99 CH.sub.2 CHCH.sub.2                                                                             CH.sub.3     108                                        II-100                                                                               C.sub.6 H.sub.5  CH.sub.3     150                                        II-101                                                                                ##STR531##      CH.sub.3     116                                        II-102                                                                                ##STR532##      C.sub.2 H.sub.5                                                                             146                                        II-103                                                                               C.sub.2 H.sub.5  H             68                                        II-104                                                                               CH(CH.sub.3).sub.2                                                                              H            105                                        II-105                                                                                ##STR533##      H             79                                        II-106                                                                                ##STR534##      H            162                                        II-107                                                                               C(CH.sub.3).sub.3                                                                               H            194                                        II-108                                                                                ##STR535##      CH.sub.3     111                                        II-109                                                                               CH.sub.3         CH.sub.2 OCH.sub.3                                                                          104                                        II-110                                                                               CH.sub.3         CH.sub.2 OC.sub.2 H.sub.5                                                                   102                                        II-111                                                                                ##STR536##      CH.sub.2 OCH.sub.3                                                                          102                                        II-112                                                                                ##STR537##      CH.sub.2 OC.sub.2 H.sub.5                                                                   119                                        II-113                                                                                ##STR538##      N(CH.sub.3).sub.2                                                                           130                                        II-114                                                                               NH.sub.2                                                                                         ##STR539##  186                                        II-115                                                                               NH.sub.2                                                                                         ##STR540##  165                                        II-116                                                                               NH.sub.2                                                                                         ##STR541##  186                                        II-117                                                                               NH.sub.2                                                                                         ##STR542##  267                                        II-118                                                                               CH.sub.3         OCH.sub.3    144                                        ______________________________________                                    

The compound of Example (II-118) disclosed in Table 4 (above) can be prepared as follows: ##STR543## 50.2 g (0.33 mol) of hydrazino-formic acid phenyl ester (=1-phenoxycarbonyl-hydrazine) and 36.6 g (0.33 mol; 90% purity) of O,O,N-trimethyl-iminocarbonate are mixed at 40° C. with 100 ml of 1,2-dichlorobenzene, and this mixture is then stirred for two hours at 60° C. Thereafter the mixture is heated further up to 120° C., while methanol (formed during the reaction) is being distilled off. Then the reaction mixture is cooled and heated again in vacuo (0.01 mbar) to a temperature of 120° C. in order to remove any remaining volatile compounds (methanol, phenol and 1,2-dichlorobenzene) from the reaction mixture. At a temperature above 120° C. the reaction product is distilled roughly and then crystallized from toluene.

This gives 7.5 g (18% of theory) of 5-methoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-one as colorless crystals of melting point 144° C.

Example (II-119) ##STR544##

57 g (1 mol) of methyl isocyanate are added dropwise at 20° C. to 30° C. to a stirred mixture of 50 g (1 mol) of hydrazine hydrate and 200 ml of water; the reaction mixture is stirred for 2 hours at 20° C. to 30° C., end the solvent is then carefully distilled off under waterpump vacuum.

The resulting methylaminocarbonylhydrazine (H₂ N--NH--CO--NHCH₃)--82.5 g (0.93 mol)--is taken up in 800 ml of methylene chloride, and 114 g (0.88 mol) of propionic anhydride are added dropwise at 20° C. to 30° C. to the stirred mixture. The reaction mixture is refluxed for 30 minutes and then stirred at 20° C. for 15 hours. The product which is obtained in the form of crystals is isolated by filtering off with suction.

The resulting N-methylaminocarbonyl-N'-propionylhydrazine (H₅ C₂ --CO--NH--NH--CO--NHCH₃)--114 g (0.79 mol)--is added to a solution of 31.4 g (0.79 mol) of sodium hydroxide in 2.4 l of water and the reaction mixture is stirred at 90° C. for 60 minutes. The mixture is then evaporated, the residue is stirred with 300 ml of ethanol/ethyl acetate, end the mixture is filtered. The filtrate is concentrated and stirred with diethyl ether, and the product which is obtained in the form of crystals in this process is isolated by filtering off with suction.

67.4 g (67% of theory) of 5-ethyl-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 86° C. are obtained.

STARTING SUBSTANCES OF THE FORMULA (III) Example (III-1)

900 g (5.1 mol) of 2-trifluoromethoxy-toluene (2-methyl-trifluoroanisole) are heated at 100° C., and 180 g (2.54 mol) of chlorine are passed in at this temperature and with UV irradiation. Nitrogen is then blown in, and the reaction mixture is subjected to fractional distillation under reduced pressure.

As the main fraction, 425 g (40% of theory) of 2-trifluoromethoxy-benzyl chloride (2-chloromethyl-trifluoroanisole) of boiling point 110° C./100 mbar and of refractive index n_(D) ²⁰ =1.5450 are obtained.

21.0 g (0.1 mol) of 2-trifluoromethoxy-benzyl chloride and a saturated solution of 13.9 g (0.11 mol) of sodium sulphite in water are refluxed for 5 hours with vigorous stirring. After cooling, the precipitated white solids are filtered off with suction and rinsed with a small amount of ice-cold water.

After drying over phosphorus pentoxide, 26.4 g of theory) of sodium 2-trifluoromethoxy-benzylsulphonate of melting point 115° C. are obtained.

23.7 g (0.085 mol) of sodium 2-trifluoromethoxybenzylsulphonate are mixed with 35.5 g (0.17 mol) of phosphorus pentachloride, and the mixture is swirled for approx. 2 hours on a rotary evaporator at 80° C.-90° C. bath temperature. The mixture is cooled, and the phosphorus oxychloride which has formed is removed in vacuo. The residue is suspended in methylene chloride, and the mixture is poured into ice water. The organic phase is separated off, washed to neutrality, dried and concentrated.

19.0 g (81.4% of theory) of 2-trifluoromethoxybenzylsulphonyl chloride are obtained as a crude product which is sufficiently pure for the subsequent reaction to give the sulphonamide. For purification, the crude product can be taken up in methylene chloride and purified over silica gel: n_(D) ²².5 =1.4854.

205.9 g (0.75 mol) of 2-trifluoromethoxy-benzylsulphonyl chloride are introduced at 30° C.-40° C. into 1.5 l of a saturated aqueous ammonia solution, and the mixture is subsequently stirred at 50° C.-60° C. for 3 hours.

After cooling, the precipitated solids are filtered off with suction, washed to neutrality with water and dried.

136.5 g (71% of theory) of 2-trifluoromethoxybenzylsulphonamide of melting point 127° C. are obtained.

A mixture of 8.9 g (0.035 mol) of 2-trifluoromethoxybenzylsulphonamide, 3.5 g (0.035 mol) of n-butyl isocyanate, 0.2 g of diaza-bicyclo-[2.2.2]-octane (DABCO) and 150 ml of anhydrous xylene is heated at reflux temperature and a weak stream of phosgene is passed in for two hours. The mixture is subsequently stirred under reflux conditions for 30 minutes, then cooled, filtered and evaporated. The residue is taken up in methylene chloride and refiltered. The filtrate contains 2-trifluoromethoxy-benzylsulphonyl isocyanate as a crude product in a mixture with DABCO and used further as such for the subsequent reaction since partial decomposition occurs on high-vacuum distillation.

Examples of hydrazine derivatives of the formula (IX) which can be obtained analogously to Example (II-1), step 1, are listed in Table 5 below. ##STR545##

                  TABLE 5                                                          ______________________________________                                         Examples of the hydrazine derivatives of the                                   formula (IX)                                                                   Ex.                                                                            No.    R.sup.1        R.sup.2    m.p. (°C.)                             ______________________________________                                         IX-2   OCH.sub.3      C.sub.2 H.sub.5                                                                           120                                           IX-3   OCH.sub.3      C.sub.3 H.sub.7                                                                           125                                           IX-4   OCH.sub.3      CH(CH.sub.3).sub.2                                                                        127                                           IX-5   OCH.sub.2 C.sub.6 H.sub.5                                                                     CH.sub.3   100                                           IX-6                                                                                                 C.sub.2 H.sub.5                                                                           174                                           IX-7                                                                                   ##STR546##    C.sub.3 H.sub.7                                                                           180                                           IX-8   OC.sub.2 H.sub.5                                                                              C.sub.3 H.sub.7                                                                           119                                           IX-9                                                                                   ##STR547##    CH(CH.sub.3).sub.2                                                                        150                                           IX-10  OCH.sub.3      C.sub.4 H.sub.9                                                                           134                                           IX-11                                                                                  ##STR548##    C.sub.4 H.sub.9                                                                           159                                           IX-12                                                                                  ##STR549##                                                                                    ##STR550##                                                                               188                                           IX-13  OCH.sub.3                                                                                      ##STR551##                                                                               140                                           IX-14  CH.sub.2 CHCH.sub.2                                                                           C.sub.3 H.sub.7                                                                           134                                           IX-15                                                                                  ##STR552##    CH.sub.2 OC.sub.2 H.sub.5                                                                  97                                           ______________________________________                                    

STARTING SUBSTANCES OF THE FORMULA (IV) Example (IV-1) ##STR553##

6.4 g (0.05 mol) of 5-ethyl-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one are dissolved in 80 ml of tetrahydrofuran, and 1.8 g (0.06 mol) of sodium hydride (80% of substance) are added under nitrogen. After the mixture has been stirred for one hour at 20° C., 7.9 g (0.05 mol) of phenyl chloroformate are added dropwise, and the reaction mixture is stirred at 20° C. for a further 20 hours. After the mixture has been concentrated, the residue is taken up in methylene chloride, and the mixture is washed with water, dried with sodium sulphate and filtered. The filtrate is concentrated, the residue is triturated with diethyl ether, and the product which has been obtained in crystalline form is isolated by filtration with suction.

This gives 4.5 g (36% of theory) of 5-ethyl-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 141° C.

For example the compounds of the formula (IV) listed in Table 6 below can also be prepared analogously to Example (IV-1). ##STR554##

                  TABLE 6                                                          ______________________________________                                         Examples of the compounds of the formula (IV)                                  Ex.                                                                            No.   R.sup.1       R.sup.2     Z    m.p. (°C.)                         ______________________________________                                         IV-2  C.sub.3 H.sub.7                                                                              C.sub.3 H.sub.7                                                                            C.sub.6 H.sub.5                                                                     88                                        IV-3  OCH.sub.3     C.sub.3 H.sub.7                                                                            C.sub.6 H.sub.5                                                                     82                                        IV-4  CH.sub.3      C.sub.3 H.sub.7                                                                            C.sub.6 H.sub.5                                                                     84                                        IV-5  NH.sub.2      C.sub.3 H.sub.7                                                                            C.sub.6 H.sub.5                                                                     133                                       IV-6  NH.sub.2      CH.sub.3    C.sub.6 H.sub.5                                                                     82                                        IV-7                                                                                               C.sub.2 H.sub.5                                                                            C.sub.6 H.sub.5                                                                     152                                       IV-8  OC.sub.2 H.sub.5                                                                             C.sub.2 H.sub.5                                                                            C.sub.6 H.sub.5                                IV-9  OCH.sub.2 CHCH.sub.2                                                                         CH.sub.3    C.sub.6 H.sub.5                                IV-10                                                                                 ##STR555##   C.sub.4 H.sub.9                                                                            C.sub.6 H.sub.5                                IV-11 CH.sub.3                                                                                      ##STR556## C.sub.6 H.sub.5                                IV-12 NHCH.sub.3    C.sub.2 H.sub.5                                                                            C.sub.6 H.sub.5                                IV-13 CH.sub.3      CH.sub.2 C.sub.6 H.sub.5                                                                   C.sub.6 H.sub.5                                IV-14 CH.sub.3      NHCH(CH.sub.3 ).sub.2                                                                      C.sub.6 H.sub.5                                IV-15 N(CH.sub.3).sub.2                                                                            N(CH.sub.3).sub.2                                                                          C.sub.6 H.sub.5                                IV-16                                                                                 ##STR557##                                                                                   ##STR558## C.sub.6 H.sub.5                                IV-17 OC.sub.2 H.sub.5                                                                              ##STR559## C.sub.6 H.sub.5                                IV-18 OC.sub.3 H.sub.7                                                                             C.sub.2 H.sub.5                                                                            C.sub.6 H.sub.5                                IV-19 C.sub.2 H.sub.5                                                                              C.sub.4 H.sub.9                                                                            C.sub.6 H.sub.5                                IV-20 CH(CH.sub.3).sub.2                                                                           CH(CH.sub.3).sub.2                                                                         C.sub.6 H.sub.5                                IV-21 OCH.sub.3     C.sub.2 H.sub.5                                                                            C.sub.6 H.sub.5                                                                     89                                        IV-22                                                                                 ##STR560##   C.sub.3 H.sub.7 -n                                                                         C.sub.6 H.sub.5                                                                     104                                       ______________________________________                                    

USE EXAMPLES

In the following use examples, the known herbicide isocarbamide, of formula (A) below, is used as comparison substance: ##STR561##

The formulae of the compounds according to the invention used in the Use Examples are listed individually below in conjunction with the number of the Preparation Examples: ##STR562##

Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added, and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil and, after 24 hours, watered with the preparation of active compound, It is expedient here to keep constant the amount of water per unit area. The concentration of active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive. After three weeks, the degree of damage of the plants is rated in % damage in comparison with the development of the untreated control. The figures denote:

0%=no action (like untreated control)

100%=total destruction

In this test a clearly superior activity compared with the prior art is shown, for example, by the compounds of Preparation Examples 2, 6, 8, 12, 13, 16, 17, 18, 19, 20, 26, 27, 28, 29, 34, 37, 39, 40 and 133.

Example B

Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added, and the concentrate is diluted with water to the desired concentration.

Test plants having a height of 5-15 cm are sprayed with the preparation of active compound in such a way that the specifically desired amounts of active compound per unit area are applied. The concentration of the spray liquor is chosen in such a way that the specifically desired amounts of active substance are applied in 1000 l of water/ha. After three weeks, the degree of damage of the plants is rated in % damage in comparison with the development of the untreated control. The figures denote:

0%=no action (like untreated control)

100%=total destruction

In this test a clearly superior activity compared with the prior art is shown, for example, by the compounds of Preparation Examples 2, 4, 5, 6, 7, 8, 12, 13, 14, 15, 16, 17, 18, 19, 20, 26, 27, 28, 29, 30, 32, 33, 34, 35, 37, 39, 40, 126, 128 and 133.

Example C

Pyricularia test (rice)/protective

Solvent: 12,5 parts by weight of acetone

Emulsifier: 0,3 parts by weight of alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water and the stated amount of emulsifier to the desired concentration.

To test for protective activity, young rice plants are sprayed with the preparation of active compound until dripping wet. After the spray coating has dried off, the plants are inoculated with an aqueous spore suspension of Pyricularia orycae. The plants are then placed in a greenhouse at 100% relative atmospheric humidity and 25° C.

Evaluation of the disease infestation is carried out 4 days after the inoculation.

In this test, a very good activity is shown, for example, by the compounds according to the following preparation examples: 9, 12, 13, 20, 30, 31, 32, 33, 34, 35, 36, 37, 140, 145, 147, 152, 153, 154.

Example D

Pyricularia Test (rice)/systemic

Solvent: 12,5 parts by weight of acetone

Emulsifier: 0,3 parts by weight of alkylaryl-polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water and the stated amount of emulsifier, to the desired concentration.

To test for systemic properties, standard soil in which young plants have been grown is watered with 40 ml of the preparation of active compound. 7 days after the treatment, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae. Thereafter, the plants remain in a greenhouse at a temperature of 25° and a relative atmospheric humidity of 100% until they are evaluated.

Evaluation of the disease infestation is carried out 4 days after the inoculation.

In this test, an excellent activity is shown, for example, by the compounds according to the following preparation examples: 9, 12, 13, 20, 30, 31, 32, 33, 34, 35, 36, 37, 140, 145, 147, 152, 153, 154.

It will be appreciated that the instant specification and claims are set forth by way of illustration and not limitation, and that various modifications and changes may be made without departing from the spirit and scope of the present invention. 

We claim:
 1. A triazolinone of the formula ##STR563## wherein R¹ is C₁ -C₆ -alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, phenyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxycarbony) or is C₃ -C₄ -alkenyloxy andR² is hydrogen, or represents C₁ -C₆ -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy or C₁ -C₄ -alkylcarbonyl or C₁ -C₄ -alkoxy-carbonyl, or represents C₃ -C₆ -cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or C₁ -C₄ -alkyl, or represents phenyl-C₁ -C₃ -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy and/or C₁ -C₄ -alkoxycarbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl, trifluoromethyl, methyl, C₁ -C₄ -alkoxy, fluorine- and/or chlorine-substituted C₁ -C₃ -alkoxy, C₁ -C₄ -alkykithio, fluorine- and/or chlorine-substituted C₁ -C₃ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl and/or C₁ -C₄ -alkoxy-carbonyl.
 2. A triazolinone according to claim 1, whereinR¹ is methoxy, ethoxy, propoxy or isopropoxy, and R² is hydrogen, C₁ -C₄ -alkyl which is optionally substituted by fluorine and/or chlorine, methoxy or ethoxy, or represents C₃ -C₆ -cycloalkyl.
 3. A triazolinone according to claim 1, selected from the group consisting of those wherein

    ______________________________________                                         R.sup.1 represents                                                                               and    R.sup.2 represents                                    ______________________________________                                         OCH.sub.3            CH.sub.3                                                  OCH.sub.3            C.sub.2 H.sub.5                                           OCH.sub.3            C.sub.3 H.sub.7                                           OC.sub.2 H.sub.5     C.sub.2 H.sub.5                                           OCH.sub.3            CH(CH.sub.3).sub.2                                        OCH.sub.2 C.sub.6 H.sub.5                                                                           CH.sub.3                                                  OC.sub.2 H.sub.5     C.sub.3 H.sub.7                                           OCH.sub.3            C.sub.4 H.sub.9                                           OCH.sub.3                                                                                            ##STR564##                                               OC.sub.2 H.sub.5     CH.sub.3                                                  OC.sub.3 H.sub.7     C.sub.3 H.sub.7                                           OCH.sub.2 CHCH.sub.2 CH.sub.3                                                  OCH.sub.2 CHCH.sub.2 C.sub.2 H.sub.5                                           OCH.sub.2 CHCH.sub.2 C.sub.3 H.sub.7                                            ##STR565##          C.sub.3 H.sub.7                                           OCH.sub.3                                                                                            ##STR566##                                               OCH.sub.3                                                                                            ##STR567##                                               OCH.sub.3                                                                                            ##STR568##                                               OCH.sub.3                                                                                            ##STR569##                                               OCH.sub.2 COOCH.sub.3                                                                               C.sub.3 H.sub.7                                           OC.sub.2 H.sub.5                                                                                     ##STR570##                                               ______________________________________                                    


4. A triazolinone according to claim 3, wherein R¹ is OCH₃ and R² is CH₃.
 5. A triazolinone according to claim 3, wherein R¹ is OCH₃ and R² is C₂ H₅.
 6. A triazolinone according to claim 3, wherein R¹ is OCH₃ and R² is C₃ H₇.
 7. A triazolinone according to claim 3, wherein R¹ is OC₂ H₅ and R² is C₂ H₅.
 8. A triazolinone according to claim 3, wherein R¹ is OCH₃ and R² is CH(CH₃)₂.
 9. A triazolinone according to claim 3, wherein R¹ is OCH₂ C₆ H₅ and R² is CH₃.
 10. A triazolinone according to claim 3, wherein R¹ is OC₂ H₅ and R² is C₃ H₇.
 11. A triazolinone according to claim 3, wherein R¹ is OCH₃ and R² is C₄ H₉.
 12. A triazolinone according to claim 3, wherein R¹ is OCH₃ and R² is ##STR571## 